From the outside looking in is a dual-purpose interview series with former Minnesota tech entrepreneurs pursuing their startup companies elsewhere. It’s great to see homegrown talent making it happen — but why not here andwhat can we learn from their perspectives?

Hometown: Hastings, Minnesota

Location: San Francisco, California

What’s your background as it relates to Minnesota? Where are you from originally?

I lived in MN from ages 2 to 24 mostly in Hastings. I did my undergrad at Gustavus Adolphus and a masters at the University of Minnesota. I also interned and worked at IBM Rochester for 2 years. My family all still lives there.

What prompted the departure from Minnesota?

I originally moved out here the summer after grad school to do a startup and take my last course of grad school at Stanford. I’ve gone back and forth various times for a job or to work with a co-founder but my head and heart keeps me here (Valley) especially while doing a startup.

What has been your startup experience to date? What are you currently pursuing?

I’ve now gone through the Y Combinator program for my second time with my new company chart.io. In my other pursuits and knowing many other startups and small businesses I realized that everyone creates their own dashboard of graphs and measures of their company’s metrics. It always takes considerable time and focus away from what you really need to be doing. I always wished for a service I could just plug into that would allow me to make all of the analytics charts with a simple interface. Chart.io is that service.

How do you and others in your current tech community perceive Minnesota in terms of talent and potential?

To be honest its not good. As a warning of things you might find yourself saying if your startup is going to fail, Paul Graham used this quote again last night and has it written in his essay “How Not to Die“: “We’re moving back to Minnesota, but we’re going to keep working on the startup.”

He actually published that essay the day before I flew back to Minnesota while working on my first startup and it was totally right. It killed our momentum.

I think Y Combinator has now funded 3 or 4 teams of people from Minnesota and I believe all have moved back home afterward. So I think they get a reputation as being family focused (as apposed to purely business focused) people. That’s probably a good thing overall but not to investors.

What’s are some of the cultural differences you’ve seen between the two places — as it relates to early stage tech?

When I was 24 I went to my first Tech conference: MinneBar in St Paul. It was the one about 3 or 4 years ago when DHH came and spoke. I came out of there super stoked about all the cool things I’d seen and people I’d met. I loved the crowd of both tech and business focused people. I loved the entrepreneur crowd.

The trouble is that I hadn’t ever met those people before. Its a small though growing community in Minnesota. Now I’m at a coffee shop in Palo Alto and those people are all around me and events like that happen so often that if you want to even a small percentage of them you’d never get any work done. Its incredibly motivating.

Also, I once wrote a now disappeared blog post about the differences between MN and the bay area while having the typical “So what do you do?” conversation when you meet someone. Basically in MN right now saying “I have a startup.” is often met with responses like “Oh… well its a tough job market out there.” Where in CA I’ll have the same conversation with someone with an awesome job from Google or Facebook and they’ll say something like “Oh man, I’m so jealous. I’m going to be doing the same next year.”

So I think its definitely a more understood and respected profession here. Which is a very important factor because when doing a startup you often wonder “Am I crazy for doing this?” and the answer is yes you are. But if you want even a chance to succeed you need to keep motivated and fighting against the herd mentality is a difficult thing while keeping spirits up.

What is your opinion on the value of incubators/seed capital?

It really really depends on which one you’re talking about. This is my second time in Y Combinator and the benefits that it gives you are enormous. I don’t think they’re ready to announce any numbers on this current batch but in the last batch of Y Combinator companies 72% of them were profitable or funded within two weeks of the program ending (a 3 month program).

Much of that is due to the quality of companies that Y Combinator accepts, but the connections, alumni network and advice are unparalleled.

I’ve heard decent things about TechStars but I don’t know of any others that have really proven themselves yet.

If a friend of yours who was still in Minnesota said he/she was starting a tech company there and wasn’t interested in moving, what advice would you give them?

If they’re married with a house and very settled there I’d understand it, but otherwise I would strongly encourage them to move out. Some people are afraid of the higher cost of living and moving to an area where they know no one. But that fear isn’t very entrepreneurial :).

If they are settled there then my advice is that they’re probably going to have to boot strap it. Read “The Four Steps to the Epiphany” by Steve Blank and see if you can keep a day job or have at-least a year of savings while you build it out.

In your estimation, what would be one thing Minnesota could do, right now, to foster a better startup culture and to retain talent?

I think the progress actually has been very impressive over the past few years. MinneDemo has become a frequent and large event. If that continues the culture will continue as well.

One thing that would really help right now is a lot of money. Its very hard to get funding for a conceptual startup in MN. So if your company needs to raise capital (and most growing companies do) you probably have to move elsewhere to find it. Paul Graham has another great essay on the subject of how to build another silicon valley.

Is there anything else you would like to add?

Some of my favorite people and best friends are Minnesotans who have moved to the bay area. Minnesota definitely raises some brilliant and wonderful people and the ones who leave the comfort of family and a good job there are often very exciting! If you’re one of those people look me up!﻿